반응 #1135526

반응 방정식

(1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-en-1-amine

dicyclopropyl ketone

acetic acid

sodium cyanoborohydride

Acetic acid

sodium cyanoborohydride

→

title compound

(1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)-N-(dicyclopropylmethyl)but-3-en-1-amine

용매

methanol

ethyl acetate

반응 조건

후처리

1. 1
   온도heating
2. 2
   workup.WAITwas continued overnight
3. 3
   세척the organic layer was washed consecutively with K2CO3 solution and sat. NaCl solution
4. 4
   건조dried over K2CO3
5. 5
   여과filtered
6. 6
   농축the filtrate was concentrated under reduced pressure at 60° C
7. 7
   기타The mixture was purified by flash chromatography on silica gel (eluent: DCM/MeOH, 95/5)

실험 절차

To a solution of 2.0 g (6.84 mmol) of (1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-en-1-amine (Example 115, Step E), dicyclopropyl ketone (7.54 mL, 68.4 mmol), and acetic acid (1.96 mL, 34.2 mmol) in methanol (25.0 mL) was added sodium cyanoborohydride (1.44 mL, 27.4 mmol) at rt. The resulting mixture was stirred at 50° C. for 2 days. Acetic acid (1.5 ml) and sodium cyanoborohydride (0.6 g) were added again and heating was continued overnight. 200 ml of ethyl acetate was added, and the organic layer was washed consecutively with K2CO3 solution and sat. NaCl solution, dried over K2CO3, filtered and the filtrate was concentrated under reduced pressure at 60° C. The mixture was purified by flash chromatography on silica gel (eluent: DCM/MeOH, 95/5) to give the title compound.

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